Take a walk down the shady streets of Chestertown. High Street, the main downtown thoroughfare, takes visitors past little shops, restaurants, and inns down to the river and the 1740s Custom House. Water Street is lined with the brick homes built by shipbuilders, lawyers, and merchants. In midtown is the Courthouse, on Cross Street, the site of a 1706 court and jail.
Behind the courthouse is the Geddes Piper House, 101 Church Alley (tel. 410/778-3499; www.kentcountyhistory.org/geddes.php), home of the Kent County Historical Society and a delightful small-town museum. The house, open Saturday and Sunday from 1 to 4pm, is a tall 1784 three-story charmer built by James Piper. Wander through the rooms to see fans, quilts, clothing, and toys from the 1880s.
How big are the trees in this old town? A giant American basswood, the state champion with a circumference of almost 17 feet and height of 108 feet, is on High Street, about a block from the river. For more foliage, check out the Virginia Gent Decker Arboretum at Washington College (tel. 800/422-1782, ext. 7726; www.arboretum.washcoll.edu). A wide variety of trees -- from Japanese pagoda to American lindens -- grow around these historic college buildings.
About halfway between Chestertown and Rock Hall is St. Paul's Church, off Route 20, erected in 1713 and one of Maryland's oldest churches in continuous use. It's open daily from 9am to 5pm; donations are welcome. The church served as a barracks for British soldiers during the War of 1812. Actress Tallulah Bankhead is buried in the church cemetery.
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